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United States Patent 3,116,284 a-(3,3-DIMETHYL-1-AZETlDINYL)-2,6-DIMETHYL- ACETANILTDE AND SALTS THEREOF Emilio Testa, San Simone, Vacailo, Ticino, Switzerland, assignor to Lepetit S.p.A., Milan, Italy No Drawing. Filed 0st. 7, 1960, Ser. No. 61,088 Claims priority, application Italy Get. 14, 1959 3 Claims. (Cl. 260-239) The present invention is concerned with a new therapeutic agent. More particularly the compound of the invention is oc- 3 ,B-dimethyl- 1 -azetidinyl) -2,6-dimethylacet anilide of the formula CH: CH: NHOOCHZN\ /O\ om CH3 0113 The new compound has been found highly eiiective as local anesthetic. Its activity has proven higher than that of cocaine and lidocaine and its toxicity is sufficiently low to allow its safe administration in man.

The following table gives the results of a comparison between isodynamic doses of zx-(3,3-dimethyl-l-azetidinyl)-2,6-dimethylacetanilide (DAD) and of lidocaine in experiments carried out on animals.

The product is preferably used in the form of addition salts with non-toxic mineral acids.

Doses are varied according to the desired efiect. In

3,115,284 Patented Dec. 31, 1963 "ice any case these doses are far lower than the corresponding doses of lidocaine.

The process for preparing the new compound comprises gradually adding to the hydrochloride of a 3,3-dimethylazetidine an equimolecular amount of a-chloroaceto-2,6- xylidide in the presence of an excess over two equivalents, and preferably 3-5 equivalents, of a tertiary aliphatic amine, such as triethylamine, in an inert organic solvent. The solution is then heated at -80" C., filtered, the solvent removed and the residue distilled in vacuo.

The following example is illustrative of the invention.

Example To a solution of 41 g. of 3,3-dimethylazetidine hydrochloride and 93 g. of triethylamine in 400 ml. of anhydrous benzene g. of a-chloroaceto-Z,6-x'ylidide are gradually added with stirring at room temperature. The solution is then heated at about C. for 5 hours, filtered and evaporated to dryness. The residue is distilled and collected at -l85 C./0.5 mm. M.P. 93-95. Yield 55 g. Hydrochloride: MP. 197.

I claim:

1. A compound selected from the class consisting of a-(3,3-dimethyl-1-azetidinyl)-2,6 dimethylacetanilide and its non-toxic mineral acid addition salts.

2. a-(3,3 dimethyl 1 azetidinyl)-2,6-dimethylacetanilide.

3. a-(3,3-dirnethy1 1 azetidinyl)-2,6-dirnethy1acetanilide hydrochloride.

References Cited in the file of this patent UNITED STATES PATENTS Schlesinger et a1 Nov. 19, 1961 OTHER REFERENCES 

1. A COMPOUND SELECTED FROM THE CLASS CONSISTING OF A-(3,3-DIMETHYL-1-AZETIDINYL)-2,6-DIMETHYLACETANILIDE AND ITS NON-TOXIC MINERAL ACID ADDITON SALTS. 